Anal

After some thought, you both decide on anal as the next challenge.

"Oh, I dunno, girl. If your sissy ass is anywhere near as tight as your throat, you're gonna have to visit the ER after I'm done with you," Bob taunts.

"Oh yeah, a nice public place where the whole world can see you together with your 'girlfirend'."

"What, you're not suggesting that I'd be embarrassed or something, are you?"

"No? Here, let's take a nice selfie together for my Instagram."

"Shit, I just remembered I wanted to see the new Star Wars movie today. C'mon, let's clean up."

You both really enjoy the movie, and surprisingly you both start crying when the the hero's boyfriend dies, getting a fair share of weird looks from the rest of the audience.

The next morning you goon for at least an hour, driving over to Bob's as soon as you're soft enough to fit back in your pants. You sneak over to his window again and see him cheating again. Good thing I cheated too.

When your friend opens the door, he's as eager to start as ever.

"C'mon, let's play! I need to know who wins!"